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Yacht sailing holidays & skippered tours in the Gulf of Naples and Amalfi Coast

Whether it is for a weekend of good food, good sea and sweet life, or for a longer trip to discover the beauty of southern Italy, the Italy, sailing vacations in Ischia, Capri, Procida and the other pearls of the Gulf of Naples the other pearls of the Gulf of Naples know how to surprise everyone.

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experiences

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The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in the Gulf of Naples and Amalfi Coast

593 reviews

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Capri Light-Blue, Positano blu-sky, Amalfi history-dreams

09/30/2024

Barbara M.

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Italy

Barca bella e pulitissima! Gennaro competente ed accogliente. La destinazione vale più giorni.
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The feast of feasts: Santa Candida in Ventotene

09/23/2024

Emanuele S.

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Italy

Non sono bravo a scrivere recensioni ma posso solo dirvi che è stata un’esperienza indimenticabile!!fare la conoscenza di Umberto vale il viaggio.
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In the blue of Capri and the infinity of the Amalfi Coast

09/22/2024

Mariarosaria B.

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Italy

Tempo non favorevole probabilmente sarebbe stato meglio annullare il weekend invece di portarci per forza a prendere freddo e mare mosso. Skipper poco organizzato nemmeno il tender ha buttato giù in mare facendoci quindi dormire in porto invece che in rada. Ho avuto esperienze migliori
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

09/18/2024

elisa b.

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Italy

Da quando ho assaporato per la prima volta la vacanza in barca a vela ho capito che non avrei più potuto farne a meno. Nello specifico questa vacanza é stata caratterizzata da un capitano davvero competente e disponibile (Andrea) nonché un equipaggio che tacitamente si é diviso le varie attività. É stato un peccato non poter vedere Capri ma il mere non lo consentiva. Le altre isole meravigliose! La barca pulita e spaziosa con una cucina super attrezzata dove la nostra deliziosa Carmen ha preparato tanti buoni manicaretti! Un’esperienza che consiglio a tutti almeno una volta nella vita!

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Guides & tips


Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Naples & Amalfi Coast: the best travel ideas

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